


Girls Will Be Girls

by samthesasquatch



Category: Supernatural
Genre: AU, Alternate Universe - 1950s, Alternate Universe - Gender Changes, Crossdressing, Destiel - Freeform, F/F, F/M, Female Castiel/Female Dean Winchester, Femslash, High School, Homophobia, Period-Typical Sexism, genderbent
Language: English
Status: In-Progress
Published: 2014-05-31
Updated: 2014-06-01
Packaged: 2018-01-27 19:17:49
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 8,101
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1719632
Author URL: https://archiveofourown.org/users/samthesasquatch/pseuds/samthesasquatch
Summary: <blockquote class="userstuff">
              <p>It's the summer of 1959 and Deanna Winchester has got it all -- looks, popularity, the perfect boyfriend...or so she thinks. When sexism begins to control her life, she throws it all away to start a new life in a new high school under the name of Dean Winchester. This is the story of how love can be found in the most unexpected of circumstances.</p>
            </blockquote>





	1. Chapter One

**Author's Note:**

> This idea has been stuck in my head for ages but I've never had the courage to put pen to paper...so here goes! Wish me luck and enjoy! ;)
> 
> Rough idea of what Deanna (pre-crossdressing) and Cassie look like: http://sam-the-sasquatch.deviantart.com/art/Girls-Will-Be-Girls-457609374

It was the summer of 1959. The sizzling asphalt became viscous in the peak heat of the afternoon sun. July had passed, moving on towards high summer; sweaty faces, buzzing flies and sweltering heat became the norm. Deanna lay sprawled on the freshly cut grass of her parents' yard in her boot-cut pants and white shirt, occassionally taking a swig from her bottle of cool coca-cola. Now, _this_ is what she called a relaxing Sunday afternoon. However, this didn't distract her from the gnawing fact that she was completely and utterly bored. There was nothing to do on days like these. Well, nothing that she enjoyed and was allowed to do. Her so-called friends were gossiping about boys and trying on each other's dresses over at Lisa's house. Well, she didn't know for sure that they were but it was a pretty good guess as it was something they did quite often.

Deanna lifted up her hand to shield her eyes from the beating sun as a shadow emerged, interrupting her thoughts as it towered over her. It was Joe Harvelle, her boyfriend. Everyone was jealous of her because of it. Joe was the school's rebellious jock. Most of the time he wore his cuffed jeans, leather jacket and greased back hairsyle. It was completely outrageous, especially because they'd recently banned denim in their high school.That was one of the things she found attractive about him. However, because of the suffocating heat, he'd left his jacket at home, donning a white vest instead.

"The guys are gonna go play some baseball, you don't mind if I join 'em do you?" he asked, looking down at her.

"No, 'course I don't mind. Can I come?" Deanna asked, picking herself up off the ground and dusting herself off.

"Oh sure, a cheerleader would be great for team morale." he nodded, raking a hand through his dirty blonde hair.

"No, I mean to play."

Joe tilted his head to the side, a look of confusion crossing his features before he burst out in to a fit of laughter. "For a second I thought you were being serious." he answered, his smile still present.

"I wasn't joking." Deanna said, folding her arms, her brow creasing in annoyance. It wasn't like she was terrible at the game, she was actually pretty good, not that they'd seen her play. Deanna believed she'd make a great addition to the team.

"Look, we've been over this before. Sports aren't for girls...it's a guy thing. Men are physically stronger...they're made for it, that's just a fact."

"That's rubbish. I'm better than half of the the boys on your team."

"Really? Then maybe I should alert the media...?"

"Get bent." Deanna spat, surprised by what she'd just said. If anyone else had heard her swear she'd have been in big trouble. Then a thought crossed her mind, did she really care? She was fed up with being treated like a lesser being just because she had boobs. Life was totally unfair. Sometimes she wished she'd been born a boy. Things would have been so much easier and maybe she could have had the chance to enjoy her life a little more instead of feeling like a bird trapped in a cage.

"Excuse me?" Joe exclaimed, raising his eyebrows, staring at her in shock.

"You heard me. Get out of my house." Deanna growled, folding her arms across her chest, her irritation increasing by the suffocating heat of the blazing sun.

"Are you being serious? What did I say?" Joe said, looking more than a little upset.

"Hey nosebleed, did I stutter? I told you to leave." Joe took out a cigarette and lit it, inhaling the smoke then exhaling through his nose, trying to act casual about the whole thing.

"Fine but don't come crawlin' back to me when you feel like you want me back, 'cause I won't be there." he replied, shaking his head as he walked over to his sleek black motorcycle.

Once he'd left, Deanna had no idea that it was going to be the last time she'd ever see him. Yelling in frustration she stormed in to the house and ran up to her room, slamming the door. She was glad her parents weren't there at the moment, seeing her like this. They'd have probably told her it was completely 'unladylike'. Her screams soon became sobs, until finally she fell asleep in to her tear-stained pillow.

When she awoke, the sun had almost set and she could feel the cool breeze seeping through the partially open window. She sighed and rubbed her eyes which were swollen from crying. Grabbing the magazine on her bedside, she flicked through it, partially interested by what the columnists had to say. However, she soon came across a review for a new movie called 'Some Like it Hot' featuring Marilyn Monroe. She looked as beautiful as ever but what really caught her attention was the comedic pair Tony Curtis and Jack Lemmon who were dressed head to toe in female attire, makeup and everything. Could she...? Should she...? Deanna jumped out of bed and glanced at her reflection, holding up her cascading golden locks so that it appeared as if she were a boy. The sight tugged the corner of her mouth in to a small smile. "Well hello, Daddy-o." she grinned. Then opening up her stupid sewing kit that she used for her home economics class at school, she grabbed a pair of scissors. Looking down at them nervously, her hand shook slightly. If she did this, there was no turning back. She could feel her heart beat painfully in her chest from nervousness. "Oh God." she muttered. Then taking a deep breath, she began to hack away in to the girly mop of hair on her head. After tidying it up a little, the pixie cut looked half decent, it actually kind of suited her. "Not bad." Deanna grinned.

Raking her hand through her hair to muss it up a little, Deanna pulled open her wardrobe and collected up all the preppy skirts and dresses... which to be honest was nearly her whole wardrobe. She then dumped it all in to a garbage bag so that she could sell them in bulk.

* * *

 

When Deanna came back in the evening, she'd spent the money she'd earnt from the clothes to buy a pair of cheap jeans and pants, two men's tops, a jacket, underwear, a pair of shoes and shades to name a few. She knocked on the front door and it was her little brother Sam who'd opened the door. "Deanna?!" he exclaimed in shock. "I'm telling Mom!"

"That's my name, don't wear it out." she muttered under her breath, rolling her eyes as she took a step inside. Her brother could be so annoying sometimes.

"Mom! Mom! You have to see this!" Sammy yelled, running in to the kitchen.

A few seconds later, Mary was pulled from out of the kitchen to see what all the commotion was about. "Oh Gosh." she exclaimed, staring at Deanna in shock. Once the surprise wore off, her mother commented, "It's actually quite sweet, darling. Very modern. The style reminds me of Audrey Hepburn."

"Really? You think so?" Deanna replied, a small smile playing on her lips. Her mother had always been kind like that. Then a thought occured to her. "Remember when I argued with you yesterday? I'm sorry...I think I've actually come around to the idea. I think it'll be good for me to have some change." she explained, tucking her hands in to her pockets. "Oh, wonderful! I knew you would. Staying at your Uncle Bobby's place really isn't that bad and the high school there has a great education system. It'll be a great experience for you and your brother...not to mention, it'll give us the space to let your grandfather stay here."

* * *

**First day at the new high school (Senior year)**

"Hurry, Deanna! We're gonna be late!" Sam yelled from the bottom of the stairs. Deanna was _always_ the late one. Not because she took long showers or anything but because she didn't wake up until _past_ the last minute. It really annoyed Sam because he hated being late. Especially on the first day of school.

"I told you to call me Dean, now!" Deanna yelled from the top of the stairs. She was having trouble hiding her... _boobs_. She hadn't really thought about it until now but she had to make it look like she was flat chested (which was going to be quite hard as she had a large pair of...yeah okay). Eventually she found some bandages in Bobby's emergency first aid kit and wrapped them around herself and fortunately, it did just the trick.

"This is so crazy. People are gonna find out." Sam called, genuinely embarrassed by the whole ordeal. If his classmates found out about his sister, he wouldn't live to see the next day. He was surprised Bobby was fine with the whole thing, to be honest. He'd said if that's what Deanna wanted to do then who was he to stop her? They didn't tell their parents though. They thought it would be best to keep it quiet.

After another three minutes and 42 seconds (Yes, Sam counted!), Dean made her... _his_ way downstairs. "How do I look?" he said, waggling his eyebrows. He was wearing the classic greaser look, shades included.

"Stupid." Sam retorted, sticking his tongue out, not wanting to admit that he looked pretty badass.

"What would I do without my little brother?" Dean joked, giving him a noogie, causing him to yelp.

"Stop! And I'm not that little."

"I disagree. 14 is basically still a baby." Dean teased, offering him a big grin. "Right. First day of school, let's get this show on the road."

They stepped out in to the crisp September air, feeling the last of the summer sun brush against their skin. Dean was still excited beyond belief that Bobby was letting him drive his 59' Chevy Impala. It was the newest model and boy was it a beast. He had no doubt they'd be jealous of it at their new high school. However, he was still nervous about taking it for a spin as he wouldn't be able to pay for the repairs and Bobby would never forgive him. Opening the door to the driver's side, he climbed in and waited for Sammy to get in before they began their 5 minute drive.

Dean pulled in to the student's parking lot and parked, double checking his appearance in the reflection of his shades before sliding them back on. By the time he had clambered out of the car, Sam had already gone to the otherside of the school, worried he was going to be late. Sometimes Dean wondered if they were even related they were so different. Smiling to himself, he slammed the door shut and trudged in to school, watching for people's reactions. As he walked through the front door, it was then that his nervousness hit full force. What if people knew straight away that he was a girl? What if he was expelled for students accusing him of being queer? He ignored his increased, painful heart rate and the sweat that had accumulated on the back of his neck and focussed his attention on finding the main reception.

He finally found it and offered a small smile to the old lady behind the desk. "Name?" she said, adjusting the antique glasses at the end of her hooked nose.

"Dean Winchester." he answered without hesitation which was when a girl roughly his age tiptoed in to the room, looking all shy and timid. She had shoulder-length black hair with bangs, startling blue eyes and a pair of cute glasses settled on her button nose. Her attire was nothing out of the ordinary, a knee-length cream plaid skirt, a navy shirt and headband. She looked like your typical straight A student. 

"Okie dokie. You're gonna have to take those shades off when you're in the school building though, son."

"No problem." Dean replied, taking them off obediently, hanging them on the collar of his shirt, revealing his warm and inviting green eyes.

"And here's your timetable and locker number. Now you best hurry or you'll miss your first lesson...which is Spanish." the woman said, adjusting her glasses for yet another time.

Damn. Dean was terrible at Spanish. He'd never really paid any attention in his past school because the teacher was just SO boring. He'd even fallen asleep one time and was sent home for it. Looking back at it though, it was kind of funny. "Thanks, m'am." he said, taking the items. Glancing at the clock on the wall, Dean turned to leave, not giving a second glance to the quiet girl in the corner who was hugging her textbooks close to her chest, waiting to receive her new timetable next.

* * *

 

 

**Spanish class**

Dean quickly serveyed the room and saw that there were three seats left. Two at the back and one at the front. He elected to sit at the desk by the window in the back row. Much to his surprise, the girl from the main office took the seat beside him. He hadn't thought he was going to see much of her. "Hey." he whispered, offering her a small, welcoming smile.

The girl turned to face him, a look of confusion crossing her features like she was surprised that he was talking to her. "--Hello?" she replied timidly.

"Name's Dean." he added.

"Cassie."

"Nice name, suits you."

"You think so?" she said, tilting her head to the head slightly. This new guy was strange. Greaser guys, or the 'cool' kids never really gave her much notice. She'd just come to school everyday, participate in the lessons and leave, not really talking to anyone. They always thought of her as a geek because of her passion for learning and reading. Maybe he was only talking to her because he hadn't figured out what she was yet. Cassie placed her textbook, notepad and pencil on the desk just as the spanish teacher glided in. She was a curvy hispanic lady who appeared to be in her mid-thirties. A wolf whistle was heard from the middle row which earned a couple of giggles from the class.

"Settle down, class." the teacher ordered as she turned around to write down her name on the chalk board. "Me llamo Señora Cruz...and as today is the first class, you're going to do some easy speaking practice with the classmate beside you. Okay, let's go." she instructed, taking a seat as the class began to talk with each other. Cassie glanced at Dean who sighed as the announcement was made.

"Let's get this over with." Dean said, turning his chair to face her. "Just so you know I can't speak Spanish to save my life."

"Está bien. Te puedo ayudar."

"I have no idea what you just said."

Cas laughed a little and shook her head. "Alright, how about we start simple. ¿Cómo te llamas?"

"Dean?" he answered, his expression doubtful.

"That's right." she grinned, adjusting her glasses. "Now you try."

"¿Cómo te llamas?"

Cas cringed at the pronounciation but didn't mention it. "Me llamo Cassie."

"Do people call you Cas for short?"

"No."

"Can I?"

"I guess."

"Cool."

"Right, let us try something harder..."

"You mean above pre-school level?" Dean grinned.

Cas giggled. "Maybe...I wouldn't want to challenge you." 

"Ohh!" he said, feigning a look of hurt. "How could you?" he joked.

"¿Cuántos años tienes?" 

"Sí, porfavor?"

"Close." Cas grinned. 

"Really?!"

"No."

"Oh." Dean pouted.  


"I asked you how old you were."

"Ah...soy ochenta." 

"You are the number eighty?"

"Oops." Dean cringed. 

"I think you mean 'Yo tengo dieciocho años."

"Prob'ly. It's no use...my spanish vocabularly is very limited. I know fiesta and siesta."

"Because those two things are very important."

"Exactly! Someone who understands me."

Cas smiled softly, her eyes locking on to his. She swallowed nervously and said "You know...if you ever need a tutor or anything...I'd be glad to help. It would also help me with my revision."

Dean raised an eyebrow and pondered for a moment. "Sure, I'm up for that. I wouldn't want to have to repeat the year." he replied, eyes locking on to hers. 

Cas quickly averted her gaze, her face flushing slightly as she gave him a small shy nod. "Great." 

**_  
_**

 

 

 

 

 

 

 


	2. Chapter Two

**Summary for the Chapter:**

> Castiel gossips with her sister Gabrielle. Dean learns the first lesson of American Football.

**Notes for the Chapter:**

> Thanks for your kind responses on my first chapter! This is my first Destiel fanfic and I honestly think I'm going to love it. I've really started to get in to this story. Thanks again for the feedback!

The cafeteria was a dull, monotonous repetition of lunch trays and superficial chatter. The strong smell of who knows what permuated through the air straight from the kitchen and a faint buzz came from the flickering artificial light in the far corner of the room, just above where Cassie sat opposite her adopted sister Gabrielle Novak. She was taking a bite out of a Hershey's bar. It was still a mystery to Cas how Gabi could live on a strict candy diet and not become overweight. She supposed it was high metabolism. Though, Gabi wasn't by any means a slender girl like Cas...curvy was probably the right word to use.  
  
Cas was picking at her dry PB&J sandwich nonchalantly when Gabi spoke up, "Who's that?" she said, nodding over to Dean who had already found and been accepted in to the popular kids' group. They were all chatting and having fun which just made the Novak's look even more pathetic, sitting here on their own with hardly anything to say.  The Novak's were quite an isolated family, not really interested in the buzzy social life of an average high school teen.  
  
"Dean. He's new." Cas answered with a shrug, taking off her glasses and wiping them with the edge of her navy shirt before resting them back on to the bridge of her petite nose.  
  
"He reminds me of James Dean. Huh...Dean...James Dean. That can't be a coincidence!" Gabi giggled, wiping her chocolate mouth with her sleeve which made Cas wrinkle her nose in disgust. Gabrielle often behaved like she didn't have a care in the world which sometimes made her appear like she didn't have any manners.  
  
"I suppose. He's in my Spanish class, we were actually partnered up today." Cas added, not meaning to sound boastful but doing so put a smile on her face. She hoped she wasn't starting to like this new guy.  
  
"Wow! I'm jealous. He looks good enough to eat." Gabi murmured, sending Cassie a wink.  
  
"You're so vulgar." Cas replied, rolling her eyes, placing the crust and remainder of the sandwich in to her paper bag. She didn't feel that hungry.  
  
"I'll take that as a compliment."  
  
"Only _you_ would find a compliment in that."  
  
"That's what makes me so unique. So, what's this Dean-o like then?" Gabi asked, her mouth still full of mushed up chocolate.  
  
"Funny?" Cas offered. "I guess he's friendly too...and a bit bizarre but he seems like a generally optimistic person. He kind of gives off that feeling, you know?"  
  
"Just my kind of man." Gabi replied, wiggling her eyebrows. "I bet he's a fan of Elvis and owns a sleek black motorcycle. Oh, and in his spare time he feeds the homeless and -- "  
  
"So that's what you dream about? Now I know what it's like inside that mind of yours and you do realise he's not competing for the Miss America pageant, you know." Cas giggled, interrupting Gabi's waffling.  
  
"A girl can dream." she sighed, finishing off the last of the chocolate and chucking the wrapper in the garbage can beside them.  
  
Just then the bell rang for the final lesson of the day. All seniors had to do sport; the girls cheerleading and the guys football. Cas wasn't by any means the best cheerleader as she never really enjoyed sports. She was more of a bookworm and she liked it that way. Books were the fountain of knowledge. If she felt like learning about something new all she had to do was pick up a book. Or, if she wanted to know what it was like to live someone else's life, she just had to read a fiction novel. Books were like portals to other worlds where Cas could be anyone or anything.  
  
Dropping the paper bag in to the garbage can, Cassie and Gabrielle made their way to the girls' changing room.  


* * *

This had to be the most nerve-wracking moment of the day. All the boys were practically _naked_ in the locker room and Dean either had the option to wait for everyone to leave before getting undressed himself or try and find a cubicle. Finally, he made the decision to make a quick beeline through the barechested men and thankfully found a couple of cubicles at the end of the corridor. He slipped in to the one on the left and locked the door.

The room was filthy. Sweat permanently clung to the air and the place smelt like the inside of Sam's sock (and trust me, that is _not_ something you want to smell). Dean pinched his nose to avoid the odour while he got changed as  just one whiff of the room made him want to gag. He donned the school's football uniform pads, pants, knee protectors, socks, boots and shirt, and left the helmet for last. Once he was done, he raked a hand through his greased back hair and unlocked the door, stepping outside. How did guys put up with this football gear? He was already sweating from it and the weight was incredible. Dean hoped he'd get used it. Putting his helmet on, he followed the rest of the guys on to the field.  
They started with basics warmups which seemed easy enough...nothing Dean couldn't handle. The tackling practice was the hard part though as he'd never had a chance to have the training the others did. Additionally, she was no where near as strong as the other men. However, what Dean was lacking in the strength department, he gained in agility and speed. Unfortunately though, he'd been partnered with Michael for the tackling exercise. Michael was your stereotypical blonde jock whose muscles had muscles. Dean swallowed nervously as Michael towered over him. The fact that the jock was offering him a friendly smile didn't change a thing, he was still just as terrifying.Dean took a few steps back until he was standing on the mark. He took his stance and was about to block Michael when a glimpse of Cassie caught his eye. She was in her cheerleader's attire, a white sweater and pleated red skirt. Her eyes locked on his for a moment and while he was distracted, Michael decided it was the right time to tackle him.The wind was knocked out Dean's chest and he flew backwards, smashing on to the cold hard ground. "Christ..." he coughed, wincing in pain.

* * *

Cassie's eyes lit up brightly when she spotted Dean on the field. He might've been one of the smallest there but he sure looked like he was capable of taking them on. Her smile widened once his eyes fixated on hers but it soon turned in to an expression of shock as Michael ploughed in to him like a boulder. She yelped and shut her eyes tight. "Oh Gosh...is he alright? I can't bear to look..." Cas asked Gabi who was chuckling to herself.

"Yeah, he's fine. Gonna have some nasty cuts and bruises though." she replied, still laughing lightly.

"I think it might have been my fault. I distracted him." Cas admitted sheepishly.

"Well, as they say, no pain no gain." Gabi said, poking her sister in the ribs. "C'mon, let's get back to practice."

* * *

 

Dean took a couple of deep breaths before he heard the coach yell "Come on, Winchester! We haven't got all day." Dean huffed and slowly picked himself up off the ground, stumbling slightly. God...he was going to be so sore in the morning. "I'm good. Let's go again." he announced, turning to face Michael. It was now his turn to start. Dean eyed his target with determination and counted down from three before charging in to the looming tower of a man. Michael pushed back harder but Dean stayed rooted in position and shoved furiously back into him with even more force. The jock stumbled backwards, off balance. "Yeah! Who da man?!" Dean yelled, fist pumping the air only to be tackled off his feet again by Michael. Dean yelped and face planted in to a murky puddle. **Lesson number one, don't turn your back away to celebrate a pre-emptive victory.**

At the end of the session, Dean was cold, humiliated and there wasn't inch of his body that wasn't in agonising pain but despite this, he felt ecstatic. That was the most fun he'd had in years. Being given the opportunity to play an active sport for the first time gave him a new sense of freedom that he thrived for. He couldn't wait to play again.

After getting changed back in to his normal attire and shoving the football kit in to his locker, he made his way in to the parking lot where he spotted Cassie two cars over. She hadn't noticed him until the girl eating some sort of candy out of a bag, nudged her. Cas' eyes flickered over to him and she glanced back down at the floor shyly. "How d'you find the lesson?" Dean asked, popping open the trunk of Bobby's Chevy Impala.

"Better than you, I think." she answered, a gentle smile blooming on her flushed face.

"Yeah, a shower and several bags of frozen peas are in order I think."

"Did you play much football in your old school?"

"Not exactly. Today was my first day." he laughed, placing his textbooks in the trunk of the car.

"Really? Not bad, then."

"Well, at least I can use it as an excuse for my poor performances in the next few weeks." he said, slamming the door shut. At that moment, he heard Sammy's voice and turned around. "Hey, kiddo." Dean greeted but he just had a grunt in response as Sam climbed in to the passenger's seat. "That was my moody brother, Sam." he explained.

"Aren't they all at that age? But you're lucky. I've got four siblings and they drive me crazy." Cassie admitted, feigning a look of exasperation. "There's Michael, Lucifer, Anna, Gabrielle and me."

"Gabrielle's me!" Gabi interjected, her head sticking out of the window of her car.

"Michael's your brother? He's...one hell of a guy." Dean commented, letting out a small laugh.

"Yeah. I saw him tackling you on the field. Sorry about that."

"So, how come there's three of you in the same year?" he asked, curiosity getting the better of him.

"I'm adopted, Gabi's our age and Michael was held back a year."

"Ah, that explains a lot." Dean replied with a curt nod.

"Anyway, our parent's are expecting us to be home soon so..."

"Yeah, it's getting quite late. See you around." Dean retorted, sliding on his shades.

_**  
**_


	3. Chapter Three

**Summary for the Chapter:**

> Dean has his first english lesson but gets both Cas and himself in to trouble.

**Notes for the Chapter:**

> I have so many things I want to write down but I have to wait until the right time of the story to put it in...so frustrating! I can tell you though there's some exciting stuff on it's way ;)

**The next day**

The sound of squeaking shoes and gossiping teens reverberated through the hallway as Dean dug through his locker for his copy of Shakespeare's 'As You Like It'. Chuck, one of his new friends which he'd met yesterday, stood patiently beside him, leaning against the locker, wolf-whistling as one of the preppy junior's sauntered past them, textbooks hugged to her chest. Dean rolled his eyes, a small smile plastered on his face. "Can't you control yourself? That's the third girl today and it's not even first period yet." Dean chuckled, slamming his locker shut as he picked up the play.

"What? She was totally stacked and it distracts me from the crushing feeling that every teacher has already told me that if I don't buck up soon I'm going to flunk all of my subjects. It's only the second day of the term!"

"That's got to be a new record, right?" Dean laughed. "If you don't watch it, you're gonna be spendin' all your free time in Mills' office."

"Oh yeah? She's gonna wish she'd never met me."

"Is that so? And what are you gonna do?"

"I'm not gonna take any of her crap. I don't take no crap from nobody."

"Chuck?" Prinicipal Jody Mill's voice rang from behind them. How long had she been standing there?

"Speak of the Devil." Dean coughed under his breath.

"Oh, Hello ma'am." Chuck answered curtly.

"Aren't you supposed to be in first period now?"

"I was just going to the little boys' room."

"Both of you? Looks to me like you were just dawdling."

"No ma'am. Yes, ma'am."

"Are you going to stand there all day?"

"No ma'am, I mean yes ma'am I just..."

"Which is it?"

"No ma'am."

"Perfect. Then get going!" she ordered, strutting back to her office, clipboard in hand.

"Yes ma'am."

"I'm sure glad you didn't take any of her crap Chuck, you really told her off, huh?" Dean snickered.

"Shut it." Chuck grumbled as they both made their way to English.

* * *

 

As the pair walked in to class, ghostly faces turned to face them, void of energy and life. The room was as silent as a morgue which meant one thing only...they'd turned up to the right room. It was Mr.McLeod's English class. However, he was more commonly known as Crowley to the students he teached. "Ah, looks like you've decided to join us boys." he announced with his thick english accent, turning to face them. "Hurry up and take a seat. I haven't got all day."

"Yes, sir." they muttered in unison, scrambling to get the only spare seat at the back. They fought for the space for a couple of seconds before Dean shoved Chuck backwards, sliding in to the seat first, grinning from his small victory. Chuck cursed under his breath. "What was that, Mr.Shurley?" Crowley asked, holding a hand to his ear.

"Nothing, sir." Chuck grumbled, grabbing one of the stacked chairs by the wall and dragging it towards the teacher's desk. He couldn't believe he was going to have sit there, right at the front of the class under the strict supervision from one of the most terrifying teacher's in school. Chuck sent Dean a deadly glare, making the eldest winchester let out a stifled laugh.

"Settle down." Crowley instructed, his tone seeping with authority.

Dean slouched back in his chair and soon recognised the girl who was sat in front of him. How could he forget those ebony locks that brushed against her shoulders. It was Cassie, he had no doubt. He tapped the back of her chair with his foot, making her turn around. "Hey." he whispered, making sure he wasn't heard by Crowley.

Cas gave him a small smile in acknowledgement but didn't answer him. She didn't want to be caught red-handed by Mr.McLeod of all people. He was known for racking people's knuckles with a ruler if they weren't paying their full attention. Cas ripped a piece of paper from the corner of her notebook and began writing a message for Dean.

_Can't talk. How about we meet up at lunch? We could go to the diner down the road._

She folded the slip neatly and passed it over to him.

"Now, where was I? Ah, yes. 'As You Like it' was a play composed by William Shakespeare. It tells the story of Rosalind who disguises herself as a man so that her true identity wasn't discovered by the people of Arden. However, that wasn't the only reason, was it? People who read the book over Summer Vacation like I had instructed will know the answer. Who can suggest another reason as to why she chose to disguise herself this way? How about...Dean?" Crowley asked, his beady black eyes fixating on the boy who wasn't paying any attention.

Dean unravelled Cassie's note and began to read, smiling at her curly handwriting. It was the neatest handwriting he'd ever seen and it completely reflected her personality: studious, shy and unique.

"Dean?" Crowley said, more forcefully this time.

Cassie turned around and tapped Dean's desk, desperately trying to get his attention.

"Huh?"

"Sorry, was I disturbing you?" Crowley replied sarcastically. Walking over to Dean's desk, he picked up the slip of paper and read it out loud to the class. "Aww."

Dean's face flushed bright red, slipping further down in his seat, attempting to disappear.

"How about you two lovebirds go to the Principal's office at lunchtime, instead? Won't it be romantic...but first, answer my question, Dean."

Cas whimpered, her face growing hot from embarrassment.

"What was the question?" he asked, swallowing nervously, feeling the hairs on the back of his sweaty neck prickle.

"Can you suggest another reason as to why Rosalind chose to disguise herself as a man?"

It was crazy to think that Crowley knew something about his own façade but Dean felt like that it could be possible. It was unnerving. Dean squirmed in his seat and chewed is lower lip thoughtfully. "I guess...because...men have more power and authority than women. Not to mention, freedom. And I guess, that's what made the disguise so appealing to her."

Crowley narrowed his eyes but eventually nodded. "Correct...you're off the hook this time, Winchester."

* * *

 

It was midday and Dean was already slouching in the rough, itchy seat outside Prinicpal Mills' office, waiting for the yelling that awaited him. It was then that Cassie glided in, all nervous and timid. She gracefully took the chair beside him, making sure to avoid his eyecontact. She was still incredibly embarrassed by the whole ordeal.

"Sorry." Dean muttered, breaking through the silence. He scratched the back of his neck nervously, hoping that he hadn't ruined the friendship they'd created by getting them both in trouble.

"Don't be. I was partly to the blame. I should have known better."

Dean placed his hand gently on hers, his fingers brushing lightly against her soft skin. Cassie's head snapped around to face him, surprised, the touch sent a light shiver down her spine. When he'd noticed what he was doing, he quickly pulled away, placing his hand back on his lap. "I...uhh...it's your first time being sent to the office though, I'm guessin'? So I guess it does mean it's my fault. But...I would have said yes anyway, if that's any consolation."

"Yeah, it's my first time. I've always been wary of the rules." Cas admitted, hoping that it didn't make her sound like the shy little school girl she was. "Yes to what?" she asked, adjusting her glasses, her brow furrowing in confusion.

"Goin' to the diner." Dean replied buntly, shrugging as he tried to look casual about it.

"Oh." Cas said, the corner of her mouth tugging upwards slightly.

"I mean, we don't have to...only if you want to...but, we could go some other time." Dean couldn't have sounded more awkward if he'd tried. There was something about Cas that made him want to impress her. His brain was in constant overdrive, always trying carefully to articulate the perfect sentences for her.

"Sounds good. How about Friday?" she asked, her sharp blue eyes settling on his own green hues. The connection gave Dean a new sense of vitality; it was as if her soul was feeding his. For a few moments he was too distracted to answer her question, but then the creak of the principal's door opening, snapped him awake.

"Friday? Cool--"

"Winchester and Novak, you may see me now." Prinicpal Mills' called from inside her office.

The two trudged inside side by side, standing in front of the principal's neatly arranged desk. In entering, the strong scent of overpowering perfume and cheap coffee hit Dean's nostrils, making him wrinkle his nose in disgust. He felt the strong need to jump over her desk and pull open the windows to take the breath of fresh air he needed so badly. Sadly, he didn't though as he stood patiently waiting for the lecture they were about to recieve.

"I hear you were sending notes to each other in class."

"It was just one t--"

"Don't answer me back, Dean."

"Sorry, ma'am."

"As it is only the second day of the term, punishment will be a mere detention after school of thirty minutes."

"I was the only one who was writing notes though, ma'am. I swear...I was gonna give 'em to Cassie it's true but I didn't get the chance, so can't you just punish me instead?"

"How noble to take the fall but I honestly doubt that it was the case."

"It was, wasn't it?" Dean said, nudging Cas in the ribs, indicating for her to just go with it.

"I...I...yes. It's true." Cas stuttered, sending Dean a confused glance. Why would he take the fall for her? She deserved the punishment just as much as he did.

"You do realise that this will mean you get double the time, Winchester?"

"Yes, ma'am." 

"Right. Well, I'll see you after school in my office for an hour."

"Yes, ma'am."

"Right, now run along. I've got paperwork to get through before the end of the day."

The two nodded, leaving the room and shutting the door behind themselves.

Cas looked up at Dean all doe eyed, her soft lips parted slightly, not sure what to say.

"Don't worry about it. I've already got the rep of getting in to trouble...there wouldn't be any point of taking you down with me." he confessed.

She had to admit it made sense but she was still puzzled by his kindness. She'd never met a guy like him...a guy who was considered to be top of the hierarchy at the school, that was this generous. "Thank you. I really appreciate it." Cas smiled. "I better go find Gabrielle...I usually meet up with her for lunch. She'll be wondering where I am." she added, offering him a small wave before turning to leave, her long skirt swishing around her knees as she strolled down the corridor.

"Don't mention it." Dean mumbled, barely audible as he watched her leave.

_**  
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	4. Chapter Four

**Summary for the Chapter:**

> Dean and Cassie's first 'Not-Date' at the Diner.

**Notes for the Chapter:**

> I'm so excited! I can finally mention some awesome 50's hits. I hope you enjoy this chapter...I wanted to introduce the idea that Dean was leading Cas away from her shy exterior, allowing her to be herself. 
> 
> N.B. I have been and will continue to use 50's slang, just FYI. E.g. Slurg = Milkshake

**Diner - Friday**

It wasn't a date. It was just two friends spending their lunch break together. That's what Dean told himself, anyway. The place was like every other diner in America. It had bubblegum colored furniture, great milkshakes and a kick-ass jukebox. As it was Friday, the place was pretty packed but they didn't mind. It really just enhanced the atmosphere of the place. Thankfully, the diner smelt good too, unlike Principal Mills' office, it had a freshly grounded coffee aroma mixed with grilled burgers. Perfect.

"You know what I think?" Dean said, sliding in to the booth bench opposite Cassie.

"What?" she said, her chin balancing on the palm of her hand.

"You need to...what's the word? Relax more, I guess...have some more fun in your life." he commented as he glanced down at the menú on the sterile diner table.

"I _do_ have fun and I _am_ relaxed." she answered stiffly.

"Prove it."

"How?"

"After we've taken our orders, I'll tell you." he answered, wiggling his eyebrows.

"You're very mysterious, Dean Winchester."

"Aren't I just?" he grinned, sliding the menú over to Cas. While her eyes skimmed over the options, he began to make a plane out of the paper napkins.

"What's that?" Cassie asked with curiosity, placing the menú on the table. Dean seemed to be making some sort of shape out of the tissues but so far it didn't resemble anything at all.

"It's a plane. See, these are the wings." he pouted, chucking it in to the air but to his dismay it just dropped back on to the table in front of him.

"Do me a favor. Don't become an engineer." she giggled, undoing Dean's masterpiece and folding it again before letting it fly. This time it glided through the air, landing on the waitresses tray. Cas raised an eyebrow, as if to say, 'And that's how it's done.'. 

"Show off." Dean grumbled but a small smile tugged on the corner of his lips.

The waitress coughed, grabbing their attention. "May I take ya order? And this is yours, ain't it?" she asked, placing the paper plane back on their table, causing them both to laugh a little. a de

"Yes, that's ours. Sorry." Cassie apologized, her face flushing a deep crimson.

"Not a problem, honey. I thought it was kinda good." the waitress explained, making Dean roll his eyes. "I guess I'll have a small vanilla slurg and apple pie." he told her. Just thinking about the pie made him drool. He hadn't had one in ages and couldn't wait to taste the fresh foamy cream against the warm crust. Pure heaven.

"Sorry, we only have large milkshakes."

"Oh, I guess I--" he began but Cas interrupted him mid-sentence, saying "That's fine. We can share, I was going to order the same thing." 

"Alright-y. Anythin' else?" she said, blowing a bubble out of gum. 

"Yeah a burger, please." Cas ordered. She adored them. Wait, no, adored wasn't the right word. She was  _addicted_ to them. They were easily her favorite food despite the fact they were supposed to be incredibly unhealthy for you and weren't exactly a gourmet meal. Her parents thought disapprovingly about them. They were nice people but sometimes their upper class status really bugged her. They would constantly belittle people around them, not that they intended it to be that way, it was just how they were brought up, she supposed.

Once the waitress left with their order, Dean stood up, holding out his hand for Cassie to take. Her eyes flickered down to his outstretched hand, wondering what he was planning on doing. Deciding to trust him nonetheless she slipped her petite hand into his surprisingly smooth hand and was led to the jukebox. "Right. You told me you were one to have loadsa fun, right? Now you can prove it. Choose a song." Dean explained, slipping on his shades as he leaned against the side of the jukebox.

Cas wondered what he was up to. Why would choosing a song prove that? Nonetheless, she glanced over the choices, smiling at the ones she recognized. "Got one." Cas announced. "Johnny B. Goode by Chuck Berry."

Dean raised his eyebrows. "Seriously? Now that's what I'm talkin' about. I was pretty sure you were going to choose somethin' by the Chordettes or the like. I guess I was wrong about you, Cassie." he said with a dimpled smile, slotting a nickel in to the machine. As the song started, Dean copied the riff with his air guitar, earning a soft giggle from Cas. "You told me you knew how to have fun, so c'mon. Dance with me." Dean said, holding out his hand, wiggling his fingers.

"No, I couldn't possibly...people will stare."

"Are you tellin' me, you're embarrassed? Look, they're not even paying attention." Dean explained, his eyes scanning the diner, noticing that only a couple of people were sneaking a glance at them.

"But I don't know how to dance..." Cas said, desperately trying to find an excuse.

"Pfft. What a loada rubbish. Everyone can dance." Dean answered and taking her hand, he spun her around, the movement causing her skirt to swish around her knees. Cas looked stunned for a minute before her look of surprise became a contagious smile.

"Come on, Miss Novak. Let's see your moves." he grinned, pulling her so close that he could smell her familiar scent of lavender. It took a few moments but soon Cas let herself relax in to the music. She began to sway her hips in time and did the occasional hop to the beat, oblivious of the onlookers in the diner. It wasn't like she was a complete embarrassment when it came to dancing, because she'd had some 'Swing' classes at school so she knew the basics but she'd always been wary of what people thought of her and always accordingly. Forgetting about all of that, she let Dean spin her around as he danced in synchronization with her. "We're putting Fred Astaire to shame." Dean commented. 

"You wish!" she exclaimed, her voice slightly breathless as Dean quickly put in another nickel in to the jukebox and selected the all-time favorite "Rock Around The Clock". "May I have this dance, my lady?" Dean bowed. 

"You may, kind sir." she replied, taking both his hands, her feet tapping to the beat. "One, two, three o'clock, four o'clock, rock!" Cas sang, surprising Dean by her sudden outgoing nature. 

"Five, six, seven o'clock, eight o'clock, rock..." Dean sang back, copying Cas as she began dancing the Lindy Hop. "Who'd have thought you were such Broadway material?" he teased, mixing in some Charleston moves, trying to impress her as Cassie spun around him. 

"You're such a tease." she replied, propping her glasses back on to the bridge of her nose. Her little distraction however, made her trip over Dean's fast moving feet, causing to her yelp. Much to her surprise though, he'd caught her just in time, dipping her as if it were a planned dance move all along. "Good reflexes." Cas commented, giggling nervously as she found her feet again.

"I like to think so." he replied, his stomach grumbling. "Oops, guess I'm hungrier than I thought." Dean said, smiling sheepishly. 

"Speaking of which, there's the waitress with our food."

"Great timing..." Dean remarked.

They began to dig in to their food almost instantaneously, their hunger intensified by all the effort they had put in to the dancing. "Man...this is delicious. I could eat this everyday...no doubt." Dean mumbled, his mouth full.

"You're disgusting." she smirked.

"You know what they say, all the best people are."

"That's not a thing. No one says that." 

"They will now." Dean replied, watching in amusement as Cassie rolled her eyes, shaking her head.

"So, tell me something about yourself, Dean." she drawled, changing the subject.

"Like what?"

"What's you favorite band?"

"Elvis, for sure." 

"Gabi was right...I don't suppose you feed the homeless and own a black motorcycle too?"

"No, why? Do I look like the kind of guy who would?"

"Something my sister said." Cas said, waving her hand dismissively.

"What's _your_ favorite band, then?" Dean asked, shoving a new spoonful of pie in his mouth.

"Would it be totally cliché to say Elvis, too?"

"Prob'ly." Dean answered, his eyes crinkling from the smile that was plastered on his face.

"But I'll listen to anything really." she mentioned, leaning across the table, reaching for the milkshake that was strategically in the middle. To her surprise, it was at that same moment that Dean had decided to take a sip too. Her soft lips parted, letting the straw slide out of her mouth as their eyes met for a fleeting moment, noses but an inch from each other. Closing his eyes, Dean cupped her face, tucking a lose strand of her hair behind her ear as he leaned closer, firmly yet gently pressing their lips together, his senses succumbing to the sweet taste of vanilla. Once the sensation ceased, Dean's eyes snapped open, the crushing realization of what he'd just done hitting him full force. He pulled away from her quickly, placing enough dollars on the table for both of their meals. "I...I can't do this...it's not right...I can't be here." he explained, his voice wavering slightly. Before Cassie could even get a word out, he ran out of the diner in to the street and out of sight.

Cas stared at the empty seat in front of her, tears welling in her eyes. She slipped off her glasses and roughly wiped away at her sore eyes. What had she done wrong? Was it the kiss? Was it really that bad? What was she thinking, kissing him like that? He'd probably kissed plenty of other girls and there was Cas the little innocent girl that she was, having just kissed for the first time. It was pathetic. She should just stick to her textbooks and be done with it. Guys like him never fell for girls like her. She shoved her glasses back on and stormed out of the diner, sighing with relief as the crisp September air whistled past her flushed face.

_**  
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End file.
